Triethylamine → N-[6-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]norbornan-2-yl]pyrrolidine-1-carboxamide

HRID 527091

Reaktionsgleichung

Reaktionsgleichung von HRID 527091
[F:1][C:2]1[C:3]([NH:18][CH:19]2[CH:24]3[CH2:25][CH:21]([CH2:22][CH:23]3C(O)=O)[CH2:20]2)=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[NH:10][CH:9]=2)=[N:6][CH:7]=1.C([N:31]([CH2:34]C)CC)C.N(P(OC1C=CC=CC=1)(OC1C=CC=CC=1)=[O:40])=[N+]=[N-].[NH:55]1[CH2:59][CH2:58][CH2:57][CH2:56]1>C1COCC1>[F:1][C:2]1[C:3]([NH:18][CH:19]2[CH:24]3[CH2:25][CH:21]([CH2:22][CH:23]3[NH:31][C:34]([N:55]3[CH2:59][CH2:58][CH2:57][CH2:56]3)=[O:40])[CH2:20]2)=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[NH:10][CH:9]=2)=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 123414Diphenylphosphoryl azideHCID 672850466-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]norbornane-2-carboxylic acid2×

Produkt 1

HCID 67285331N-[6-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]norbornan-2-yl]pyrrolidine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a solution of 6-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]norbornane-2-carboxylic acid, 72j, (0.030 g, 0.078 mmol) in THF (0.375 mL) was added triethylamine (0.032 mL, 0.234 mmol) and (azido(phenoxy)phosphoryl)oxybenzene (0.018 mL, 0.085 mmol). The reaction mixture was heated to 95° C. for 2.5 hours, cooled down to 5° C., and treated with pyrrolidine (0.010 mL, 0.117 mmol). The reaction was stirred for 3 days at room temperature. The reaction mixture was injected directly into a preparatory HPLC system for purification to provide the product as a racemic mixture. The single enantiomers were obtained by separation using SFC chiral purification to afford 5.7 mg of the desired product as well as 1.4 mg of the enantiomer.

Aufarbeitung

  1. temperaturecooled down to 5° C.
  2. customThe reaction mixture was injected directly into a preparatory HPLC system for purification
  3. customto provide the product as a racemic mixture
  4. customThe single enantiomers were obtained by separation
  5. customSFC chiral purification

Quellen und Nachweise

ORD-Eintrag
ord-a340cc9616014a4caacf52f8e46d37fa
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345708B2

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